


The Fall of a Player

by Buildyoudown



Category: Supernatural
Genre: Alternate Universe - High School, Betrayal, Explicit Language, Flirting, Heart Break, M/M, Mind Games, Pining, nerd!cas, player!dean
Language: English
Status: In-Progress
Published: 2015-09-28
Updated: 2016-01-20
Packaged: 2018-04-23 18:46:52
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 3
Words: 8,554
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4887826
Author URL: https://archiveofourown.org/users/Buildyoudown/pseuds/Buildyoudown
Summary: <blockquote class="userstuff">
              <p>Dean and his friends play a bit of a messed up game. The rules are simple. Here's your target, your mission is to sleep with them as quickly as possible. But when Deans new target is Castiel Novak will he be able to follow through? And when Castiel finds out the truth will he ever be able to forgive Dean?</p>
            </blockquote>





	1. Chapter 1

"So who's next?" Dean Winchester asked picking at the fries on his plate.

"Not sure yet." Gordon said absentmindedly scanning the crowd of teenagers eating their lunch. 

"Would you mind giving me a challenge this time, that last girl was way too easy." Dean said with a smirk. 

"Yeah, yeah, yeah, I'm sure she was." Gordon said rolling his eyes. Dean grinned and sat back looking around. "Oh, I got the perfect guy." 

"Who's that?" Dean asked interested, usually Gordon picked girls for Dean, very few guys. 

"Castiel Novak." He said smiling smugly. Dean searched his memory trying to place the name. The name brought a face to the surface, they might have had a class together last year. They have at least two this year. He was cute but in a subtle way, he didn't talk a lot but you could tell he was smart. There was an air about him, or maybe it was his glasses. Ok so maybe Dean had noticed him before.

"Dark hair, bright blue eyes, kinda dorky?" Dean asked a face coming to him. Michael snorted.

"Yeah that's him, loser if I ever saw one but not too bad on the eyes." 

"If you think he’s so dreamy you take him." Dean said. 

Michael punched his arm, "You got your target, now go do your worst." 

"Alright, alright." Dean said. He scanned the cafeteria for a minute before spotting the guy sitting at the other end of the cafeteria and shared his table with with a red haired girl, Anna Milton; and a Dark haired girl, Meg Masters. How he managed to befriend Meg Masters was beyond Dean, she was the exact opposite of him. Castiel was quiet and kept his head down, Meg was outspoken and would flirt with anyone who she figured worthy. He waited for his table to clear, Meg stood up a few minutes later to talk to another one of her friends and Anna left to use the restroom or throw away her food, it didn't really matter. Either way he had his chance. "Ok I'll see you in a minute." Dean said to Michael and made his way across the large room.

Castiel was sitting on his phone while he ate French fries. He jumped a little when Dean startled the chair next to his. 

"Hello?" he said confused.

"Hey" Dean said with his most flirtatious grin, "Castiel, right?" 

"That's correct" He said slowly.

"I'm Dean." 

"Okay." Castiel said 

"Wonder how I never noticed you before." Dean said letting his eyes drag over Castiels frame. He wore a button down and jeans. His hair was a crazy mess but undeniably hot. Dean watched as he squirmed a little under his gaze, grinning at his slight discomfort.

"Don't have faintest idea" Castiel said sounding indifferent but the blush that spread across his cheeks told a different story. 

"See you around Cas" He said grinning and winking at him. 

"It's Castiel." He muttered.

"Sure thing, Cas" Dean called behind his shoulder as he left.

 

"This is going to be a piece of cake" Dean said with a laugh as he joined his friends again. 

 

-|||-

 

Dean was walking down the hall to his designated class room for free period when he caught a glance of familiar dark hair in the library. He grinned at the perfect opportunity and made his way to class to tell his teacher he was going to the library. He really didn't want to get another detention they were so dull. When he walked back into the library Castiel was nowhere to be found but a bag that Dean recognized as his had been moved to one of the back tables. Dean threw his bag down and waited for him to come back from wherever he was. About one minute later he heard a voice from above him.

"Why are you sitting here?" Dean looked up and saw an annoyed looking Castiel tilting his head at him. 

"Do you have a problem with me sitting here?" Dean answered him. He narrowed his eyes but didn't push it, instead he sat down and pulled his book closer to him. 

"So you got any plans this weekend?" Dean asked pulling Castiels book toward him. Castiel tried and failed to grab his book but Dean held it tight. He pursed his lips and took a deep breath.

"Look Dean, I know what your plan is and I don’t want any part in it" He started to say more but Dean interrupted.

"And what’s that?" How much did he know about their game? 

"You’re all players who don’t care at all about the people you happen to be dating. It’s odd and I don’t want to be just another name off a list" Castiel continued. Dean was about to interrupt him again but Cas, as Dean had decided to call him, held a finger up and continued to talk. "So I would appreciate if I didn't get dragged into these foolish primitive games." 

"You done?" Dean asked. Most people didn’t react this way toward his advances, he prided himself on shutting down the hostility people had toward him, but not Castiel. It was actually pretty hot.  _Wait what?_  Dean thought, he didn't think this way about the people he seduced, he just didn't what was this guy doing? Cas tilted his head a little before saying that yes he was done. "You're right my friends and I used to play those games a while ago but I'm over it, it was immature and I don’t know you seem great." He finished his quickly fabricated lie with a small smile.

"I'm sure you are done but it's going to take a lot more than your word to prove you're done whoring around. I'm not just going to lay there and do whatever you say." Castiel said grabbing his book back and opening it again.

"Fine, I'll prove it, prove how serious I am about dating you." Dean said, he had asked for a challenge and that's just what he got.

"Just so you know even if you do succeed in pestering me enough to go on a date with you, I still won't let you fuck me in the back of your car after just one small dinner." 

"Oh we'll see about that." He winked and sat back.

 

He ended up sitting there watching Castiel as he read, he glanced up a few times shifting under his unbroken stare. He didn't have to add that last comment and because he did it just made it seem like Castiel was going to crack a lot sooner than Dean anticipated

"Are you going to stop staring at me?" He asked quietly a blush coming up as he talked.

"Nope." Dean said grinning in amusement. 

 

-|||- 

 

The next day he walked over to where Cas parked his car and waited for him to get out.

"Hey." He said and reached into his car to pull out his bag. 

"What are you doing?" He asked narrowing his eyes. Deans grinned subconsciously because that eye narrowing was just really damn cute. He scolded himself for thinking that and went back to his normal exterior. 

"Just thought I'd walk you to class." He threw the extra bag over his shoulder and turned to start walking.

"Okay. What are you doing with my bag?" 

"I'm carrying your bag." He said with his best award winning smile. Castiel cocked and eyebrow

"I am fully capable of carrying my bag, thank you." He said making a grab for it. But Dean jerked his arm and held it behind him out of Cas' reach. 

"I'm aware you  _can_ carry it but you aren't going to." He turned and walked around Castiels car forcing him to walk the other way to keep up with him.

"Why are you doing this?" He asked again trying to grab his bag but Dean managed to keep it out of his reach. 

"I told you already, I like you." Dean lied easily. He said it so easily he almost thought he wasn't lying, maybe he had been doing this too long.

"I still don't believe you." He grumbled and crossing his arms, refusing to look or talk to him now. He may be a little more difficult than Dean was used to but he sure was cute and would probably be good in bed, even with his virgin air this could be worth more than just a hook up.

After they walked into the school Dean continued walking leading the way to where he knew Castiels homeroom to be.

"How do you know where my homeroom is?" He asked suspicious. He kept walking ignoring his question.  "Are you a stalker or something?"

"You sure do ask lot of questions." 

"Yeah, I'm not used to random guys coming onto me out of the blue, I tend to have a few questions." Cas said.

"You know I wasn't expecting you to be so snarky." Castiel snorted.

"Snarky, really that's how you would describe me." 

"Oh, definitely." 

 

He dropped Cas off at his homeroom and refused to leave even after Castiel told him countless times he was just going to study. So Dean sat there staring at him like an idiot for the next twenty minutes. He couldn't stop himself from thinking how much he actually enjoyed just sitting there watching him study. It was strange, he wouldn't do this for anyone else. He chalked it up to just being because Castiel was a tough and he wouldn't be able to do the same thing he always did.

Dean was relieved Castiel and most of the student body didn’t know about his friend’s game, sure they knew he slept around a lot or dated a lot but they didn’t seem to realized that they were just another check on his list. Cas did say that’s what he wanted to be though, which just added to what made Castiel special. His friends, Gordon, Uriel and Michael had dragged him into it. At first it kept him up sometimes how badly he was treating people but eventually he learned to ignore it because his friends had pushed him into and there were expectations he had to uphold. And now all those feelings were coming back now that he was thinking about it. He had gone so long just focusing on the fun he was having instead of the damage he was causing.

Eventually he did have to leave to go to his homeroom. He stood up started to say good bye to Castiel, but he didn't acknowledge him.

"Cas?" He whispered drawing out the S in his name. But he must be too engrossed in what he was reading. So Dean leaned forward and kissed his cheek to get his attention. It worked, Castiel jumped back looking surprised. 

"What are you doing?" He said alarmed. Dean laughed at how intensely he had reacted.

"I just kissed your cheek." He said. 

"I-I know but I- just no one’s done that before." He said quietly before dropping his sentence and shifting uncomfortably in his seat and looking away from Deans gaze.

"Hey," Dean asked reaching down to tilt Castiels head to look him in the eye. He smiled trying to get him to look at him. "You okay?"

"I am, it just surprised me that's all." He said finally looking up at him.

"Well as long as you aren't insulting my kissing skills." He tried to joke. Which Cas scoffed at.

"I would hardly count that as a kiss, there wasn't a lot of skill to insult you on."

"I could give you a real kiss you know, show you some real skill." Dean said with a wink as he stood to leave, it seemed to fluster Cas which, wasn't his intent but it was shockingly endearing. 

 

-|||- 

 

The first time he could 'accidently' run into Castiel was around fourth bell. If Dean went the opposite way than he normally did he could catch up to Castiel and walk with him for a little. He did that and when he caught up to him he was already walking with some random guy. He was a little annoyed but realized that was ridiculous and set his shoulders to walk up to his other side.

"Hi Cas." He said smirking at him, "Who’s this?" he nodded at the guy on his side.

"My friend Balthazar, we were just going over something our teacher said." He said turning to his friend to introduce him to Dean. Whoever he was, he wore a tight white t-shirt, which was cut way too low to be tasteful, and when he talked to Dean he had a British accent. Dean could only scoff internally at Balth-whatever his name was. He obviously thought he was so much cooler than he was (even though all he did was greet Dean). All Dean did to acknowledge his greeting was to tilt his head at his before turning his attention back to Castiel. 

"So did you get the notes for Chemistry?" 

"I did." He answer slowly. 

"Do you think I could borrow them, I seem to have misplaced mine?" Dean asked smiling at him brightly. 

"Oh, uh sure I'll give them to you in English." He said almost sarcastically like he knew Dean was bullshitting him.

"You're a true lifesaver Cas. I'll see you in English."  Castiel just smiled and turned his attention to his friend while Dean took stood by his side, feeling a little foolish. He was hoping for him to at least pay a little more attention to him. He shrugged before turning and walking back the way he came.

 

-|||- 

 

One of the tactics Dean sometimes used on people who weren’t all that interested was to just stop talking to them for a few days. They would get so used to him talking to them that when he suddenly stopped they would be desperate for the attention again. Well in theory. Since Castiel seemed less than interested in Dean he figured this would help him out some. So the next day he didn’t talk to him in class, he ignored him in class and didn’t try to catch his eye in lunch. Michael did nudge him at some point and tell him ‘That guy you’re hooking up with is staring at you’ but when he turned around Castiels gaze had dropped. He couldn’t help but grin at this observation, hoping it meant he was wondering where he had been. He even kept the notes he had borrowed just so Cas would have to talk to him at some point if he wanted them back.

And as it turned out he did, two days after he had stopped talking to him Cas finally approached him in class. Out of the corner of his eye Dean could she Castiel sitting on the edge of his seat like a bird about to take flight, biting his lip. Debating whether or not to get up. He jumped up suddenly and walked over to Dean.

“I need my notes back.” He said very suddenly but added on when he saw Dean slowly turn his gaze up

 “Sure.” He said calmly and a little amused reaching into his bag and pulling out the meticulously organized and typed out notes he had borrowed. 

“You could have given them to me when you were done.” He heard Cas mutter to himself as he grabbed his notes.

“Sorry didn’t catch that Cas.”

“It’s Castiel.” He said leaving in an annoyed huff.

 

After a four days the only contact the two had had was intense staring contests across class rooms (usually embarrassingly interrupted by a teaching) and the cafeteria, most of which ended with Cas dropping his gaze blush filling his face. That Monday he walked up to Castiel in the parking lot again but before he could say anything Cas turned around. He jumped before realizing who it was. Then he rolled his eyes and let out a hard breathe.

“Go away.” He said simply closing his car door hard and walking away.

“Hey, what’s wrong?” Dean called after him.

“You don’t get to ignore me for a week and just talk to me again out of the blue.”

“Did you miss me?” Dean said an arrogant smile gracing his face.

“Don’t flatter yourself. I simply have no interest in playing this game, like I said!”

“Look, I’m sorry. I just thought you didn’t have any interest in me so I figured I’d give you a chance to come to me not the other way around.”

“I don’t have any interest in you and don’t try and make this my fault, that’s some manipulating bullshit.”

“Fair enough.” Dean said walking a little quicker to get in front of him. “Just give me another chance.”

“Another chance? What is that even supposed to mean. You just need to send clear signals instead of screwing with me, like I may add is exactly what you do when are playing a game with someone. Like I knew you were doing.” He took a deep breathe at the end of his rant.

“Okay I won’t do it again.”

“Good.”

“So will you go to dinner with me?”

“Screw off.”

“Oh come on. It’ll be completely platonic, and I’ll pay. It’s my way of making up for being a jerk.”

“Why don’t you just bring me take out. That sounds a lot easier. And doesn’t paying still make it a date?”

“It’s a date.” Dean said as they got into the building and Dean split off from Cas.

“I wasn’t being serious Dean!” Castiel yelled after him. But his words were useless, Dean already had a plan.

 

-|||- 

 

“So how’s Castiel doing?” Gordon asked at lunch that day.

“Fine, as far as I know.” Dean answered picking at his food.

“How close are you to finishing up?” Michael asked joining the conversation. Dean took his time answering not really sure how to. Maybe he wasn’t ready to be finished.

“Uh, I’m not sure he’s doesn’t seem very interested but you know how that normally goes. So it could go either way.”

“That didn’t make any sense.” Gordon said

“I have a plan this weekend and I’ll see what happens.” He said hoping to finish this conversation up. He didn’t like the way Gordon and Michael were referring to Cas like he was a school project that just needed to be finished up. It had never bothered him before, this is how they talked. It just seemed different this time. “So how’s Lea? Is that her name?”

“Lenore actually but whatever. Man you don’t even know.” He launched into a very detailed description of the things he and Lenore had done the pervious Saturday. Which apparently involved doing it on most of the surfaces of an abandoned house they had found.

 

-|||-

 

He found Cas in the library their free period that Friday and walked over to join him. Pulling the book away from him just like he had that first day, but Dean totally wasn’t thinking about that.

“Dean, what a pleasure.” Cas said dryly reaching for his book.

“You have good taste.” Dean said looking at the book in his hands.

“Thank you.” He said making another grab for his book.

“So what are you doing this weekend?” Dean asked laying the book in his lap and folding his hands on the table giving him his full attention.

“Nothing of import.” He answered squinting at him and turning his head to the side.

“I’m just making conversation, Cas.”

“I might get together with Anna on Saturday, my parents are going out of town tonight so I’ll probably stay in.”

“Sounds fun.” Dean said grinning.

“Definitely.” He said pulling out another book from his bag and opening it, making Dean laugh at his preparation. This time Dean just sat there and watched as Castiels eyes scanned the page slowly. They really were beautiful, his eyes, the perfect bright shade of blue. And when he looked at Dean it felt like he could fall into them, and contrast to his messy dark hair it made them look brighter.

“Don’t you have homework or anything you could be doing?” Cas asked shifting nervously under Deans intense stare, which seemed to be common.

“Yep, but you’re a lot more interesting.”

“I’m not even doing anything.” He muttered.

“You don’t have to do anything but sit there and look cute.” Dean said smiling proudly to himself when the blush rose on Cas’ cheeks.

 

-|||-

 

That night Dean went out and bought a bunch of takeout food from the best Chinese place in town. Then drove over to Cas’ house praying his parents had indeed left for the night. After he rang the bell he realized he was anxiously biting his cheek and had almost drawn blood. _Since when did he have nervous habits like that_ He thought to himself. Before he could contemplate it anymore the door swung open revealing Cas only wearing a pair of sweatpants that slung low on his slim hips, Dean could see his hip bones jutting out in the hottest way. And even more shockingly, he was wearing glasses, obviously he wore contacts to school but he really shouldn’t. The glasses were the hottest thing he had ever seen. It was only when Castiel said his name in confusion that he looked up.

“What are you doing here?” He asked confused. Dean just held up the bag of food smiling.

“I brought you dinner.” Cas just scrunched his eye brows together and cocked his head to the side.

“Why?” He asked slowly.

“Remember you told me to just bring you take out.”

“And then I said I wasn’t serious.” He said sounding shocked like no one had brought him dinner before. Never the less his stepped back to let Dean in.

“I hope you like Chinese.” He said giving him a half smile.

“Yeah I do. The dining room is in there,” He pointed to a room on his right, “I’m going to go-uh- p-put a shirt on.” He said

“Oh you don’t need to do that on my account.” Dean said checking him out as he walked up the stairs.

“Obviously I do.” He said. Dean’s eyes rose, he hadn’t noticed Cas had turned around and had seen him blatantly staring at him. He just laughed grinning and continued walking up stairs. Dean walked into what he had said was the dining room and set the bag on the table and started taking the containers out. By the time he had a few out Castiel had come back down. He wearing a t-shirt that was in disarray, like he had anxiously pulled it on and not bothered to fix it. His hair had also been messed up even more than when he had opened the door.

“I’ll get forks.” He said smiling quickly as he walked into what Dean assumed was the kitchen. He came back and sat down sliding a fork across to Dean and grabbing a container to start eating. “This was definitely unexpected.”

“I like to be spontaneous.” Even though that was a complete lie, he had been planning this for a few days. It was stupid and not a big deal but Dean couldn’t stop thinking about what they would talk about and what Cas’ house would look like, if Cas would act differently around him and if he possibly would let his guard down more.

“So this wasn’t planned at all?” He asked sounding suspicious.

“Uh…no.” He was a terrible liar and Dean could tell Cas knew it was planned. He just stared at his food and ate a little more. “Look if you’re uncomfortable with me being here I can leave.” He started to stand up Cas all but yelled at him.

“No!” His hand went up as to reach out to him. He cleared his throat before saying it again, “No, I appreciate this. No one’s done anything like this before so I don’t know I’m just a little nervous.”

“Well if it’s any consolation so am I.” He smiled at his food.

“Why are you nervous, you planned this?”

“Shut up,” He grumbled, “I’m in the guy I likes house for the first time and I have no idea how he’s reacting.” Castiel blushed when he said ‘guy I like’ but didn’t say anything.

“I guess I can help with that. I’m surprised but not unhappy you’re here.”

“You’re not unhappy, couldn’t you just say you’re happy to see me.” He teased.

“I could.” They sat through the rest of the meal talking easily about pointless things. And when they finished Castiel asked Dean if he wanted to watch a movie. Dean of course quickly agreed, and when he found out he hadn’t seen star wars he immediately made him watch it.

So here they were unnecessarily close to each other on the couch while star wars played on Castiels TV. He seemed to not be all that into the movie but Dean hardly noticed because he was too busy staring at Cas to ask him about him. Eventually he looked up at Dean too raising his eye brows some.

“Why are you staring at me?” He said blushing and looking away.

“Because you look really cute even in this shitty lighting.” Dean whispered and it didn’t feel like a lie

“You can’t say stuff like that.” Cas muttered.

“Why not? It’s true.”

“But it’s making me like you and I told myself I wouldn’t do that.”

“Tell yourself you’re an idiot.” Dean said quietly leaning closer. He heard Castiels breath catch in his throat anticipating Deans next move. His eyes flicked down to Deans lips and Dean surged forward pressing his lips to Cas’ eagerly, his hand going to Cas’ hair and his cheek, his glasses pushed a bit higher on his nose. Cas kissed back quickly but unsure of his movements, he wasn’t very practiced with kissing but Dean couldn’t bring himself to care, in fact it just added to how much he liked him. Cas’ hands ended up on Deans chest, his hands clutching at Deans shirt hard enough to leave wrinkles in it. He reveled in the closeness of it all but ran his hand down to Castiels back pulling them flush against each other. He needed more, he wanted to melt into Cas and stay that way forever. Dean ran his tongue over Cas’ top lip and he opened his mouth with a moan. When he pulled back a little in embarrassment Dean chased his lips and held him closer. And when they finally pulled away they leaned their foreheads together breathing heavy and hot against each other.

“Dean.” Cas panted taking his glasses off and tossing them onto the side table next to Dean.  

“Y-yeah.” He answered.

“Let’s do a lot more of that.” He said turning his head up to look at him.

“Definitely.” Dean said pulling him up so he was straddling him. Cas moved his hands into Deans hair and Dean moved his to Cas’ hips gripping tightly. Dean then moved to suck a hickey into his neck, enjoying the little moans he was emitting. After a few minutes, of what Dean would describe as the best make out session ever, Cas pushed himself back catching his breath and looked away shyly. “Hey, are you okay?” Dean reached up to touch his flushed cheek delicately. He looked truly amazing like this, spit slicked lips which were open slightly, his cheeks were red and his hair was a complete mess.

“I- I uh think you should go.” He said sounding shocked by his words.

“Wait, what?” Dean asked shocked but moved his hands off him none the less. Castiel got off him clumsily not making eye contact. “Did I do something wrong? I’m really sorry.”

“No, no nothing. You just need to leave.”

“Okay” He waited a second, “I guess I’ll see you later”, Cas’ words felt like a punch to the gut but Dean forced himself to stand, grab his jacket and leave the house. When he got into his car he hit his steering wheel, angry at himself to messing things up. He didn’t know what he did wrong but obviously it was something. And he was determined to fix it. In that moment he knew his feelings were betraying him and he was falling for him but it didn’t matter, all that mattered was making it up to Castiel.


	2. Chapter 2

**Notes for the Chapter:**

> this is so badly written im sorry

“Oh my god I’m such an idiot” Castiel groaned, his voice slightly muffled because his face was buried in hands.

“Are you ever going to tell me what happened? I never got any specifics” His best friend Anna asked.

“No”

“Oh come on you’ve been holding out on me, all I know is he started flirting with you out of the blue” She insisted. Castiel turned his head up pouting.

“Fine, he uh he came over the other night, and brought me dinner-“

“That’s so sweet!”

“Yeah but I’m not stupid he doesn’t actually like me he’s just trying to get into my pants, that’s all he ever does. I mean the longest he ever dated someone was Lisa, and even that was, what  two months? Anyway not the point, he brought my dinner, we ate, we watched a movie, we made out and I asked him to leave.”

“Whoa back up there, you’re going to need to go into that a little deeper.” Anna said. Castiel took a deep breath and sat up on his bed.

“After dinner I asked if he wanted to watch a movie, he said yes, we sat down and watched a movie, he was staring at me, like he has a habit of doing, and I asked why and he said because I looked cute and then there was a moment and we kissed. And after a little I came to my senses and realize I was letting him get to me, which is exactly what I didn’t want so I stopped and asked him to leave.”

“And did he?”

“Yes of course he’s not a complete jack ass.”

“Okay so I know you don’t trust him and that’s pretty justified but he doesn’t act like this toward everyone and he usually gives up faster than this if he doesn’t get results. So maybe he’s not lying.”

“Are you saying I should trust him and just forget about his track record?”

“Not necessarily, more like you should give him a chance and see how things turn out. But I wouldn’t suggest sleeping with him after the first date just because it’s him.”

 He didn’t respond.

“I’ll see you tomorrow I have some things to finish up for the paper.” She stood up, kissed him on the cheek and left his room.

It had been three days since he had asked Dean to leave his house and he still hadn’t heard from him, not that it’s a big deal he didn’t have his number so how would he hear from him. But he also knew he should make a move now, he was the one that kicked Dean out he should say something. But he couldn’t bring himself to. He was too afraid, afraid Dean would be mad about being asked to leave, afraid Dean will have moved on; afraid that he would laugh and say it didn’t matter, that he never mattered. He wanted to talk to him, he had wanted to talk to him since eighth grade. So knowing this was likely a plot to get him into bed hurt even more. Castiel rubbed his face and pulled his covers over his head willing himself to fall asleep. Eventually he did and only woken up by his brother calling him for dinner.

 

-|||-

 

When he pulled into school the next day and looked around, wishing Dean would materialize behind him, grab him bag and lead him inside. But he didn’t. Castiel took a deep breath and told himself he would talk to him that day. He felt someone looking at him in English and glanced over, Dean was looking at him and his expression could only be described as worried or nervous. Cas found himself smiling and then turned back to his paper. At lunch he stood up and walked over to Dean’s table, his stomach in knots. Dean was laughing at something his friend had said when he got there.

“Hey, Dean” Castiel said quietly. He turned his head and smirked up at him.

“Hey”

“I was hoping we could talk alone.”

“Okay.” He gestured to the door as he stood up, his face now unreadable. Castiel bit his lip anxiously as they walked into the hall. When he turned to face Dean his whole demeanor had changed. He looked nervous now instead of his usual cocky. “Castiel I am so sorry about the other night, I didn’t mean to push you the way I did. I didn’t know what to say to you so I just thought I would give you some space.” Oh god he was being so sweet and gracious thank god.

“It wasn’t you really I just sort of freaked out” He smiled sheepishly, “So does that mean you aren’t mad at me?”

“Of course it wouldn’t be fair of me to mad at you for something like that.”

“Good, I didn’t really want you to be mad at me.” He said to his shoes.

“Are you flirting with me?” Dean teased, laughing a little.

“Of course not that would be foolish.” He tried and failed miserably to sound serious.

“So does that mean you wouldn’t be opposed to going to dinner with me?”

“Maybe not.” He said quietly looking at the floor.

“Okay.” Dean said grinning happily.

“Don’t be so damn cocky.” Castiel said but couldn’t hold back his laugh. Dean just laughed and they walked back into the lunch room going their separate ways.

 

-|||-

 

Castiel really wasn’t sure what to make of Dean Winchester, they had been going to the same school since middle school but they were never friends or even acquaintances. Castiel had always had a weird awareness of him, like he was more aware of his presence and constantly keepings tabs on him when he was in eye site. He refused to acknowledge that it was a crush for the longest time but eventually he had to come to terms with it. He thought it was probably when he saw Dean kissing some girl in the hallway, and jealously had flared up in him. Even then he just kept walking ignoring the flare of pain through his gut. He never got over it, just sort of ignored his feelings willing to stop. But now that Dean was giving him so much attention he was certain they wouldn’t go away unless things progressed with Dean.

Currently Castiel was sitting in the back of the library trying to focus on his textbook but he was basically just reading the same sentence over and over. Not surprisingly Dean sat down across from him, a few seconds later he grabbed his book and pulled it over to him. Reminding Castiel of the first time they had met here.

“Physics, very interesting” He said scanning the page.

“I agree” he said smiling and trying to grab his book back. He was successful but only because Dean didn’t attempt to keep it.

“So for dinner I was thinking I would pick you up around seven?”

“What?” he said his heart picked up pace at the impending awkward conversation that was about to occur, “You do know you never actually asked me out, and just assuming I’ll go along with it is a little pretentious.”

“Fair enough.” He said looking around, the he stood and then knelt next to him, “Castiel Novak, will you do me the honor of letting me take you out to dinner tonight.”

Castiel couldn’t help but start to laugh a little but finally nodded his cheeks a little red.

 

-|||-

 

Even though it was a Monday he has still agreed to dinner, as long as he got home in time. His parents told him he had to be back by nine which was unusually accommodating. He and Dean had switched numbers before the bell had rung, so now he was constantly checking his phone for another message. Dean had texted him telling him that he would indeed get him at seven.

6:30: Castiel had changed his shirt three times and his jeans twice. He had settled on a simple blue button down and the second pair of jeans

6:45: Castiel was nervously waiting on his couch

6:57: There was a knock on the door which was eagerly answered by Castiel

7:00: Dean had said hello to Castiels parents and led him to the car

7:15: They pull into the restaurant parking lot

Dean walked around the car, opening the door for Castiel and leading him to the doors. While they walked up Dean slipped his hand into Cas’, causing him to grin and squeeze Deans hand in reassurance. Dean opened the front door letting Cas go in front of him but not letting go of his hand. The hostess smiled at them, grabbed two menus and led them to an empty table by one of the windows.

“Your waiter should be over in a moment.” She said happily. The two boys sat in silence while they examined the menus. Behind his Castiel was anxiously biting his lip and Dean was bouncing his knee violently under the table.

“What are you going to get?” Dean asked, trying to sound casual but Castiel could detect a hint of panic in his voice.

“Not sure I usually would just order a burger, but.” He trailed off.

“Yeah.” Dean whispered, more to himself. A moment later a man walked up to them holding a pad of paper.

“Hello my name is Samandriel and I’ll be your server tonight, can I start you with some drinks?” He asked politely.

“I’ll just have ice water.” Castiel said looking up him from his menu.

“I’ll have the same.” Dean said a little awkwardly. Samandriel nodded and walked away to get their drinks. Castiel set down his menu and fiddled with him napkin until Dean noticed.

“Hey, are you okay?” He asked. He reached his hand out to touch Castiels but pulled back at the last second.

“Of course.” He hesitated, “Just a little nervous I suppose, I haven’t been on a date in quite a while.”

“What happened on your last date?” Dean asked hopping it would provoke a conversation. Before he could answer their waiter came up with their water and took their orders. After he left Dean waited for him to continue his story. Castiel smiled to himself and laughed a little before answering.

“Well it was with Meg Masters, and it was in the summer before ninth grade.”

“You weren’t kidding about it being a while.” Dean said laughing.

“Don’t be rude!” He said but was grinning in spite of himself, “Anyway, we went to a dinner at that little diner on Second Street and well considering we we’re both awkward fifteen year olds it went about as well as you can expect.” He blushed lightly but continued, “And I- I tried to kiss her when we left but it was my first kiss and we both tried to go the same way and ended up hitting noses kind of hard and that was that.” They were both laughing now trying to get it under control before people started to notice.

“That’s definitely a better first kiss story than mine.”

“Oh we never actually kissed, her mom came to pick her up before I could try again.” Dean started giggling even harder at that, “My first kiss was at a party Anna dragged me too last year, she got me very drunk and I ended up kissing someone during spin the bottle, but neither of us can remember who it was. What about you who was your first kiss?” Dean answered once he had gotten his laughter under control.

“Like I said not very interesting, her name was Kaitlyn Marks and it was in seventh grade. I was over at her house, we were in her basement and I just leaned over and kissed her. But it was pretty horrible.” Just then their food came. For the rest of the night they ate off each other’s plates, stared at each other too long and played footsie under the table. When the check came Dean immediately grabbed it waving off all of Castiels attempts to split the bill. And when they leave the restaurant and find a chill has set over the city, Dean takes his jacket off and slides it over Castiels shoulders, he even thought he saw a hint of pink on Dean’s cheeks.  

 

-|||-

 

That Monday he saw Dean before Dean saw him, he was with his friends and they appeared to be arguing but he couldn’t hear anything.

At lunch he wanted to ask him about it but didn’t think they were close enough for him to ask. But Dean was sensing something was off, he kept asking if he was okay when Cas zoned out.

“Do you want to do something tonight?” He asked sounding nervous.

“Sure, what did you have in mind?” Castiel was desperate to sound casual and it appeared to work.

“Movie at mine?”

“Sounds wonderful, I’ll meet you at your house after school.” They spent lunch in a comfortable silence but for the rest of the day Cas had a gnawing feeling in his gut and he couldn’t quite put his finger on what was wrong.

 

-|||-

 

Castiels last class fairly far away from the parking lot, if not as far as you could get, so by the time he got to the parking lot, if he stopped at his locker, it was almost empty. He was putting his backpack in his back seat when it happened. Someone pushed him hard, before grabbing him, spinning him around and shoving him against the door. Gordon walker. He had Castiels sweater in a tight grip and his teeth were bared in an almost smile. After a moment Gordan released him and took a step back.

“So, you and Dean?”

“Wh-what about us.” He tried his best not to stutter but it happened anyway.

“So you’re an us now?”

“Well the way you worded it-“

“Shut up. I’m just here to deliver a little news. As you know me and my friends like to sleep around a bit, including our friend Dean. Well what you don’t know is we have a game going, we choose a target for each other and their goal is to see how fast they can seduce them. I’m going to assume tonight was going to be Deans big hit with you, literally.”

“Why should I believe you?”

“Did you really believe all those lines about being done sleeping around and wanting a real relationship? Did you seriously believe you were special? Whisper all those promises in your ear.” He must have seen the crushed look in Castiels eyes because all he did was snort and continue talking, each sentence like a punch in the gut, “Figures, we had a good laugh about that. All the most desperate targets drink that bullshit up.”

Castiel didn’t say anything

“Just figured you should know he doesn’t really care about you, you’re just another fuck to him.” And with that he turned around and walked back into the building. With shaking hands, Castiel opened his car door and sat in the driver’s seat, locking the door and trying to calm down. He wouldn’t break down, not over a boy he barely knew, and not over something that asshole told him. He would wait, confirm with Dean that Gordon was just trying to mess with him. He left the parking lot and drove to Dean’s house.


	3. Chapter 3

**Notes for the Chapter:**

> I'm really sorry its been so long since I updated. I just could not find any inspiration for this work. This is pretty short but I have some stuff I'm working on for the next chapter and I think I finally came up with a plan for what's going to happen.

Dean anxiously straightened the pillows on the couch one more time, pulling a piece of lint of one of them.

“Dude, you need to chill.” He looked up to his little brother leaning against the door frame.

“I thought you already left to go to Jess’ house.”

“I was just leaving, but I’ve never seen you look so uptight about something, you must really like this guy.” Sam walked over and sat down on the couch. Dean twisted his hands in his lap before answering.

“I just don’t want to fuck it up with this one. He deserves better than that.”

“Just be yourself, or wait scratch that maybe don’t.” Sam laughed as Dean swatted his shoulder.

“Get out here.”

“Yeah, yeah I’m going.” He laughed as he walked out the front door giving him a goofy thumbs up as he left.

It was only a few minutes later when he heard a knock at the door. He jumped up to get it, maybe answering it a little too quickly because Castiel looked a little alarmed when the door swung open.

“Hey, Cas, come on in.” He walked in offering a nervous smile. “Can I get you something to drink?”

“Yeah, just water or something.”

“Okay, well make yourself at home.” He walked into the kitchen to retrieving two glasses and filling them with water from the fridge.

Cas was looking at some of the pictures on the wall when he walked back into the room.

“Is this your brother?” He asked taking one of the glasses.

“Yeah, that’s Sam, you just missed him actually he only left a few minutes before you got here.”

“He looks nice.”

“Depends if you find snarky preteens nice.” Castiel laughed and look a sip of water, “I’m kidding, though, he’s a pretty great kid. So any movies in mind to watch?” Dean walked over to their movie case and opened it, looking through some of the CD’s.

“Can I ask you something?” Cas said quickly. Dean stood up and turned to face him, he was running his finger over the glass quickly and was biting his lip again.

“Yeah of course.”

“So before I left the school, your friend Gordon talked to me.” Dean felt the blood drain from his face, “and he told me some stuff.”

“What’d he say?” His voice was neutral somehow.

“That you were just using me as a target for some game you play.” He looked up at Dean, a kind of fear and vulnerability in his eyes.

“Shit, Cas I am so sorry it wasn’t supposed to happen this way.” Dean said as he ran his hands over his face.

“So, it’s true.” Castiel's voice cracked.

“Only in the beginning, nothing I told you was a lie, I meant it all.” He tried to walk up to Cas but he put his hand up, his eyes dangerous.

“Don’t you dare touch me. I may be quiet and seem shy or something but you will not get away with this. Bullshit you meant it, all I’ve ever been to you was a target, you don’t care. Stay the fuck away from me, or I swear you’ll regret it.” He slammed the water glass on the closest surface, water sloshing out of it and left, slamming the door behind him. Dean just stood there, staring at the place Cas had last been standing. It only took him about thirty seconds to go from shocked to heartbroken. He didn’t let it get far, just a tear or two before he walked upstairs and laid down refusing to cry. 

 

-|||-

 

Castiel returned home not twenty minutes later and immediately went to his room. He didn’t want to talk to anyone or explain anything to anyone, he just wanted to be alone. He could see how they would react if he told them what happened. Anna would tell him it wasn’t his fault, and that at least they never went too far. But if he wanted her to fully understand, he would have to tell her how hard he had fallen, and he could hardly admit that to himself. Dean had completely played him. There was no way that couldn’t be true. He had tricked him into thinking he cared and then used the most cliché line ever, “it started out that way but…” as if he would fall for that. Castiel was a lot of things but stupid was certainly not one of them.

-|||-

The next day at school he just tried his best to pretend everything was fine. He took notes, did his worksheets and made appropriate small talk, everything he could to make sure everything was fine. It was apparently working very well until Dean came up to him at lunch. He was talking with Anna about some movie she had watched that weekend when he walked up and tapped him on the shoulder.

“Hey, uh do you think we could talk for a minute?” His eyes looked pitiful like he hadn’t slept all night.

“Oh, don’t worry, I can give you guys some space.” Anna said with a smirk at Castiel. She stood up and left them alone at the table. He probably should have told at least her the truth.

“What do you want Dean.” He refused to look him in the eye, just picking at the bread roll on his plate.

“I know you hate me right now but please just let me explain. Just five minutes that’s all I need.”

“There’s nothing to explain. I know what happened.”

“I know you’re angry, you have every right to be but please just let me explain.”

“The thing is Dean, I don’t believe a word that comes out of your mouth anymore. Don’t waste your breath trying to get me too.” He stood up throwing his bag onto his shoulder. “Honestly, I just need some time before I can look at you without wanting to punch something.” With that he left the cafeteria.

 

-|||-

 

“Are you fucking kidding me?” Jo said in utter confusion to Dean as he lay face down on his bed.

“I know. It’s horrible and gross and I’m a bad person, trust me this has all hit me hard recently.”

“So your little games come back to bite you in the ass finally and you want my help out if it?”

“Please, Jo. He’s different, I liked him the minute we had a real conversation. There was just something undeniable about it.”

“Oh, but I’m sure you did your best to deny it.” She said spinning around in his desk chair. He didn’t respond. “So do you have a plan to try and win him back, or at least to get him to listen to you?”

“I tried to talk to him, he said just looking at my face made him want to punch something and he didn’t believe anything I said. I can’t do anything about that.”

“Tell me trying to explain everything was your only plan.” She stopped spinning and gave him a look.

“Well…yeah.”

“You spent the last year bullshitting your way into how many girls’ pants, but this Cas comes around and suddenly you can’t make one coherent thought. Typical boy.”

“Does that mean you’ll help me?” He tried not to sound too hopeful.

“Yes, I’ll help your pathetic pinning ass.”

**Author's Note:**

> I'll do my best to update once a week. Right now I have two and half chapters written and I'm hoping posting this will push me to write it more often. Comment and kudos if you want me to continue!


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